Straightforward and Highly Diastereoselective Synthesis of a New Set of Functionalized Dispiropyrrolidines Involving Multicomponent 1,3‐Dipolar Cycloaddition with Azomethine Ylides

The diastereoselective synthesis of novel series of dispiropyrrolidines has been achieved by a one‐pot three‐component [3 + 2] cycloaddition reaction of (E)‐2‐arylideneindanones, glycine ethyl ester, and the cyclic diketones 1H‐indole‐2,3‐dione (isatin) or acenaphthenequinone. Moreover, we disclose...

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Bibliographic Details
Published inJournal of heterocyclic chemistry Vol. 56; no. 6; pp. 1748 - 1756
Main Authors Boudriga, Sarra, Elmhawech, Besma, Moheddine, Askri
Format Journal Article
LanguageEnglish
Published HOBOKEN Wiley 01.06.2019
Wiley Subscription Services, Inc
Subjects
Chemistry
Chemistry, Organic
Cycloaddition
Diketones
Glycine
Physical Sciences
Science & Technology
Stereochemistry
Stereoselectivity
Synthesis
ANTIMYCOBACTERIAL ACTIVITY
SPIROOXINDOLE DERIVATIVES
ANTICANCER
SPIROPYRROLIZIDINES
PYRROLIDINE DERIVATIVES
AGENTS
STEREOSELECTIVE-SYNTHESIS
FACILE
DISCOVERY
PYRROLIZINE
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Summary:The diastereoselective synthesis of novel series of dispiropyrrolidines has been achieved by a one‐pot three‐component [3 + 2] cycloaddition reaction of (E)‐2‐arylideneindanones, glycine ethyl ester, and the cyclic diketones 1H‐indole‐2,3‐dione (isatin) or acenaphthenequinone. Moreover, we disclose an unprecedented epimerization of spiroadducts leading to a new family of dispiropyrrolidines with an unusual relative stereochemistry.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.3532